EP2384322B1 - Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes - Google Patents

Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes Download PDF

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Publication number
EP2384322B1
EP2384322B1 EP09799289.5A EP09799289A EP2384322B1 EP 2384322 B1 EP2384322 B1 EP 2384322B1 EP 09799289 A EP09799289 A EP 09799289A EP 2384322 B1 EP2384322 B1 EP 2384322B1
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Prior art keywords
alkyl
haloalkyl
alkoxy
group
halogen
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German (de)
English (en)
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EP2384322A1 (fr
Inventor
Klemens Minn
Hansjörg Dietrich
Jan Dittgen
Dieter Feucht
Isolde HÄUSER-HAHN
Christopher Hugh Rosinger
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Bayer Intellectual Property GmbH
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Bayer CropScience AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms

Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • optically active 2-aminopyrimidines processes for their preparation and their use for controlling harmful plants.
  • pyrimidines which have a herbicidal action.
  • EP 0 523 533 A1 substituted 4-aminopyrimidines and their use in the field of crop protection.
  • WO 2008/043031 discloses (R) -6-chloro-N 4 - (8-fluorochroman-4-yl) pyrimidine-2,4,5-triamine as a precursor to the preparation of pharmacologically active purines.
  • pyrimidine derivatives which are used as herbicides or plant growth regulators, in particular with a satisfactory herbicidal action against harmful plants, with a broad spectrum against harmful plants and / or with a high selectivity in crops can be used.
  • These pyrimidine derivatives should preferably have a better property profile, in particular a better herbicidal activity against harmful plants, a broader spectrum of harmful plants and / or a higher selectivity in crops than the pyrimidine derivatives known from the prior art.
  • new pyrimidines have now been found which can be used advantageously as herbicides and plant growth regulators.
  • the compounds of this series are characterized in addition to good efficacy and crop compatibility by cost manufacturing processes and access, since the substances of the invention can be prepared from inexpensive and easily accessible precursors and therefore can be dispensed with the use of expensive and difficult to access intermediates.
  • the compounds of the invention differ from the compounds according to EP 0 523 533 A1 in that they are optically active bicyclically substituted 4-aminopyrimidine-2-amines.
  • mR 5 is hydrogen. Further preferred is when mR 5 is hydrogen and the other radical R 4 is (C 1 -C 6 ) alkyl.
  • R 5 is hydrogen and the other radical R 4 is methyl.
  • the compound of the general formula (I) also includes compounds which are quaternized by a) protonation, b) alkylation or c) oxidation on a nitrogen atom.
  • the compounds of formula (I) can form salts.
  • Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom, for example in the case where R 1 contains a COOH group or a sulfonamide group -NHSO 2 -.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate.
  • salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts
  • R 1 to R "' each independently of one another represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts.
  • the compounds of formula (I) can be prepared by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g.
  • a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
  • radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, alkylthio, haloalkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton may each be straight-chain or branched.
  • these radicals are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in unsaturated groups having 2 to 6 carbon atoms, in particular 2 to 4 carbon atoms, is preferred.
  • Alkyl radicals including in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; wherein at least one double bond or triple bond, preferably a double bond or triple bond is included.
  • Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-ene-1 -yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl;
  • Alkynyl includes, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl.
  • Cycloalkyl groups are, for. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • the cycloalkyl groups can occur in bi- or tri-cyclic form.
  • haloalkyl groups and haloalkyl groups of haloalkoxy, haloalkylthio, haloalkenyl, haloalkynyl and the like are mentioned. are indicated in these residues, the lower carbon skeletons, z. B. with 1 to 6 carbon atoms or 2 to 6, in particular 1 to 4 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or branched. Examples are difluoromethyl, 2,2,2-trifluoroethyl, trifluoroallyl, 1-chloroprop-1-yl-3-yl.
  • Alkylene groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 10 carbon atoms, in particular 1 to 6 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples are methylene, ethylene, n- and i-propylene and n-, s-, i-, t-butylene.
  • Hydroxyalkyl groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples of these are 1,2-dihydroxyethyl and 3-hydroxypropyl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl or naphthyl, preferably phenyl.
  • compounds of the general formula (I) or their agrochemical salts or quaternary N derivatives of the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the aforementioned or mentioned below preferred meanings occur in combination.
  • this carbon atom can have both an (R) and an (S) configuration.
  • the present invention relates to compounds of general formula (I) having (R) configuration detected.
  • the present invention relates in particular to compounds of the general formula (I) in which the stereochemical configuration at the carbon atom marked with (*) having a stereochemical purity of 60 to 100% (R), preferably 80 to 100% (R), in particular 90 to 100% (R), especially 95 to 100% (R).
  • the present invention relates in particular to compounds of the general formula (I) in which the stereochemical configuration at the carbon atom marked with (*) having a stereochemical purity of 60 to 100% (R, or analog-R), preferably 80 to 100 % (R, or analog-R), in particular 90 to 100% (R, or analog-R), very particularly 95 to 100% (R, or analog-R), is present.
  • the compounds of the general formula (I) according to the invention may have further chiral centers on the carbon atoms labeled with (**) and (3):
  • any stereochemical configurations are possible on the carbon atoms labeled with (*), (**) and (3): Configuration carbon atom (*) Configuration carbon atom (**) Configuration of carbon atom (***) R R R R R S R S R S S
  • diastereomers (Z and E isomers) can occur.
  • enantiomers and diastereomers may occur.
  • Corresponding stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not specified with their specific stereoform and their mixtures.
  • Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood as a procedure, as for example by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34 is described.
  • a number of commercially available devices can be used, for example, Calypso reaction blocks (Caylpso reaction blocks) from Barnstead International, Dubuque, lowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations of Perkin Elmar, Waltham, Massachusetts 02451, USA.
  • Calypso reaction blocks Calypso reaction blocks
  • chromatography apparatuses are available, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods.
  • solid phase-assisted synthesis methods are adequately described in the specialist literature, eg Barry A. Bunin in The Combinatorial Index, Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999 .
  • the use of solid-phase assisted synthetic methods allows a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • Another object of the invention is due to the herbicidal property of the compounds of general formula (I), the use of the Compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants.
  • Herbicides are used in agricultural crops during various stages of cultivation. Thus, the application of some products already before or during the sowing. Others are applied before the crop is run, ie before the seedling reaches the surface of the earth breaks through (pre-emergence herbicides). Postemergence herbicides are finally used when either the cotyledons or leaves are already formed from the crop.
  • the compounds of the invention can be used both in the forerun and in the wake, wherein a use of the compounds of the invention in the flow is preferred.
  • Pre-emergence treatment includes pre-sowing (ppi) pre-sowing treatment as well as treatment of sown, but not overgrown crop areas.
  • the compounds of the formula (I) according to the invention and their salts, also referred to below together as compounds of the formula (I), have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.
  • herbicidal activity in dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium are observed.
  • the compounds of general formula (I) according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops such. As wheat, barley, rye, rice, corn, sugar beet, cotton, oilseed rape and soy only insignificant or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.
  • the substances of the general formula (I) according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, such as, for example, B. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Other special properties may be in a tolerance or resistance to abiotic stressors z. As heat, cold, drought, salt and ultraviolet radiation.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY ; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 ,
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA for the purpose of achieving a cosupressing effect or the expression of at least one corresponding thereto engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • the compounds of the general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth substances, such as B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • the essential plant enzymes eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds of the general formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • Injection powders are preparations which are uniformly dispersible in water and, in addition to the active ingredient, also contain ionic and / or nonionic surfactants (wetting agent, dispersant) in addition to a diluent or inert substance, eg.
  • Example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine.
  • the herbicidal active compounds for example, in conventional apparatus such as hammer mills, blower mills and Finely ground air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent z.
  • organic solvent z As butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products
  • alkyl polyethers sorbitan esters
  • sorbitan esters such as e.g. B. sorbitan fatty acid esters or Polyoxethylenensorbitanester such.
  • Dusts are obtained by grinding the active ingredient with finely divided solids, eg. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids eg. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally added surfactants, such as. B. are already listed above in the other formulation types, are produced.
  • Emulsions eg. As oil-in-water emulsions (EW) can be, for example, by means of stirring, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as. B. are listed above in the other types of formulation produced.
  • EW oil-in-water emulsions
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for.
  • adhesives for.
  • polyvinyl alcohol polyacrylsaurem Sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying fluidized bed granulation
  • plate granulation mixing with high-speed mixers and extrusion without solid inert material.
  • spray granules see, for. B. Procedure in " Spray-Drying Handbook "3rd Ed. 1979, G. Goodwin Ltd., London one; JE Browning, "Agglomeration”, Chemical and Engineering 1967, pages 147 ff ; " Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57 ,
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I).
  • the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating aids, fillers and the like are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent-based agents, fillers, carriers and colorants, defoamers, evaporation inhibitors and the pH value and Viscosity-influencing agent.
  • the compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) with other pesticidal substances, such.
  • pesticidal substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators combined.
  • Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants.
  • the weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, especially 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.
  • the formulations present in commercially available form are optionally diluted in a customary manner, for.
  • emulsifiable Concentrates emulsifiable Concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the type of herbicide used u.a. varies the required application rate of the compounds of general formula (I). It can vary within wide limits, eg. B. between 0.001 and 10.0 kg / ha or more active substance, but it is preferably between 0.005 and 5 kg / ha.
  • connection description 1.27 firmly; logp (HCOOH): 2.77; 1 H-NMR (CDCl 3 , 400 MHz, ⁇ in ppm): 1.25 (d, 3H, CH 3 ); 2.25 (m, 1H, 1H of CH 2 ); 2.30 (s, 3H, CH 3); 2:35 (s, 3H, CH 3); 2.50 (dd, 1H, 1H of CH 2 ); 3.05 (dd, 1H, CH); 4.40-6.40 (m, 4H, NH 2 , NH, CH); 6.95 - 7.10 (m, 3H, Ar-H) 1.30 firmly; Mp .: 197.7 ° C; logp (HCOOH): 1.39; 1 H-NMR (DMSO, 400 MHz, ⁇ in ppm): 1.20 (d, 3H, CH 3 ); 2.25 (m, 1H, 1H of CH 2 ); 2.30 (s, 3H, CH 3); 2.30 (s, 3H, CH 3);
  • Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with addition of 0.2% wetting agent applied.
  • ABUTH Abutilon theophrasti
  • ALOMY Alopecurus myosuroides
  • AMARE Amaranthus retroflexus
  • CHEAL Chenopodium album
  • CYPES Cyperus esculentus
  • ECHCG Echinochloa crus-galli
  • LOLMU Lolium multiflorum
  • MATIN Matricaria inodora
  • POLCO Polygonum convolvulus
  • PHBPU Pharitis purpurea
  • SETVI Setaria viridis
  • STEMS Stellatia media
  • compounds of the invention have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds.
  • the compounds of Table 1 have very good herbicidal activity against harmful plants such as Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Amaranthus retroflexus and Alopecurus myosuroides pre-emergence at an application rate of 0.32 kg and less active ingredient per hectare.
  • Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
  • compounds according to the invention have a good herbicidal postemergence activity against a broad spectrum of grass weeds and weeds.
  • the compounds of Table 2 have very good herbicidal activity against harmful plants such as Echinochloa crus-galli, Abutilon theophrasti, Amaranthus retroflexus postemergence at an application rate of 0.32 kg and less active ingredient per hectare.

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Claims (19)

  1. Composés optiquement actifs de formule générale (I) et leurs sels acceptables sur le plan agrochimique,
    Figure imgb0035
     dans lesquels
    R1 et R2, indépendamment l'un de l'autre, sont choisis dans le groupe constitué par
    - hydrogène, halogène, hydroxy, cyano, nitro, amino, C(O)OH, C(O)NH2 ;
    - (C1-C6)-alkyle, (C1-C6) -halogénoalkyle, (C1-C6) alkylcarbonyle, (C1-C6)-halogénoalkylcarbonyle, (C1-C6) -alkylcarbonyloxy, (C1-C6)- halogénoalkylcarbonyloxy, (C1-C6)-alkylcarbonyl-(C1-C4) -alkyle ;
    - (C1-C6)-alcoxy, (C1-C6)-halogénoalcoxy, (C1-C6)-alcoxycarbonyle, (C1-C6)-halogénoalcoxycarbonyle, (C1-C6) -alcoxycarbonyl- (C1-C6) -alkyle, (C1-C6) - halogénoalcoxycarbonyl-(C1-C6)-alkyle, (C1-C6)-alcoxycarbonyl-(C1-C6)-halogénoalkyle, (C1-C6)-halogénoalcoxycarbonyl-(C1-C6)-halogénoalkyle ;
    - (C2-C6)-alcényle, (C2-C6)-halogénoalcényle, (C2-C6)-alcénylcarbonyle, (C2-C6)-halogénoalcénylcarbonyle, (C2-C6) -alcényloxy, (C2-C6) -halogénoalcényloxy, (C2-C6)-alcényloxycarbonyle, (C2-C6)- halogénoalcényloxycarbonyle ;
    - (C2-C6) -alcynyle, (C2-C6) -halogénoalcynyle, (C2-C6)-alcynylcarbonyle, (C2-C6)-halogénoalcynylcarbonyle, (C2-C6) -alcynyloxy, (C2-C6) -halogénoalcynyloxy, (C2-C6)-alcynyloxycarbonyle, (C2-C6-halogénoalcynyloxycarbonyle ;
    - tri-(C1-C6)-alkylsilyl-(C2-C6)-alcynyle, di-(C1-C6)- alkylsilyl-(C2-C6)-alcynyle, mono-(C1-C6)-alkylsilyl- (C2-C6) -alcynyle, phénylsilyl- (C2-C6)-alcynyle ;
    - (C6-C14) -aryle, (C6-C14) -aryloxy, (C6-C14)-arylcarbonyle et (C6-C14)-aryloxycarbonyle, qui peuvent à chaque fois être substitués sur la partie aryle par halogène, (C1-C6)-alkyle et/ou (C1-C6)-halogénoalkyle ;
    - (C6-C14)-aryl-(C1-C6)-alkyle, (C6-C14) -aryl- (C1-C6) alcoxy, (C6-C14)-aryl-(C1-C6)-alkylcarbonyle, (C6-C14) -aryl- (C1-C6) -alkylcarbonyloxy, (C6-C14) -aryl-(C1-C6) -alcoxycarbonyle, (C6-C14) -aryl- (C1-C6)-alcoxycarbonyloxy ;
    - mono-((C1-C6)-alkyl) -amino, mono-((C1-C6)-halogénoalkyl)-amino, di-((C1-C6)-alkyl)-amino, di-((C1-C6)-halogénoalkyl) -amino, (C1-C6) -alkyl- (C1-C6)-halogénoalkyl)-amino, N- (C1-C6)-alcanoyl)-amino, N-((C1-C6)-halogénoalcanoyl)-amino, aminocarbonyl-(C1-C6)-alkyle, di-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyle ;
    - mono-((C1-C6)-alkyl)-aminocarbonyle, mono-((C1-C6)-halogénoalkyl)-aminocarbonyle, di- (C1-C6)-alkyl)-aminocarbonyle, di- (C1-C6)-halogénoalkyl)-aminocarbonyle, ((C1-C6)-alkyl-(C1-C6)-halogénoalkyl)-aminocarbonyle, N-((C1-C6)-alcanoyl) -aminocarbonyle, N-((C1-C6)-halogénoalcanoyl)-aminocarbonyle ;
    - (C1-C6)-alcoxy-(C1-C6)-alkyle, (C1-C6) -alcoxy- (C1-C6) -alcoxy, (C1-C6) -alcoxycarbonyl= (C1-C6) -alcoxy ;
    - (C3-C8)-cycloalkyle, qui peut le cas échéant être substitué sur le radical cycloalkyle par (C1-C6)-alkyle et/ou halogène ; (C3-C8)-cycloalcoxy, (C3-C8) -cycloalkyl- (C1-C6) -alkyle, (C3-C8) -cycloalkyl-(C1-C6) -halogénoalkyle, (C3-C8) -cycloalkyl- (C1-C6)-alcoxy, (C3-C8)-cycloalkyl- (C1-C6)-halogénoalcoxy, (C3-C8)-cycloalkylcarbonyle, (C3-C8) - cycloalcoxycarbonyle, (C3-C8)-cycloalkyl-(C1-C6)-alkylcarbonyle, (C3-C8)-cycloalkyl-(C1-C6)-halogénoalkylcarbonyle, (C3-C8)-cycloalkyl-(C1-C6)-alcoxycarbonyle, (C3-C8)-cycloalkyl-(C1-C6)-halogénoalcoxycarbonyle, (C3-C8)-cycloalkylcarbonyloxy, (C3-C8)-cycloalcoxycarbonyloxy, (C3-C8) -cycloalkyl- (C1-C6)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-(C1-C6)-halogénoalkylcarbonyloxy, (C3-C8)-cycloalkyl-(C1-C6)-alcoxycarbonyloxy, (C3-C8) -cycloalkyl- (C1-C6)-halogénoalcoxycarbonyloxy ;
    - (C3-C8) -cycloalcényle, (C3-C8) -cycloalcényloxy, (C3-C8)-cycloalcényl-(C1-C6)-alkyle, (C3-C8)-cycloalcényl-(C1-C6)-halogénoalkyle, (C3-C8)-cycloalcényl-(C1-C6)-alcoxy, (C3-C8)-cycloalcényl-(C1-C6) -halogénoalcoxy, (C3-C8)- cycloalcénylcarbonyle, (C3-C8)-cycloalcényloxycarbonyle, (C3-C8)-cycloalcényl-(C1-C6)-alkylcarbonyle, (C3-C8) -cycloalcényl- (C1-C6)-halogénoalkylcarbonyle, (C3-C8)-cycloalcényl-(C1-C6) -alcoxycarbonyle, (C3-C8)-cycloalcényl-(C1-C6)-halogénoalcoxycarbonyle, (C3-C8)-cycloalcénylcarbonyloxy, (C3-C8)-cycloalcényloxycarbonyloxy, (C3-C8)-cycloalcényl-(C1-C6)-alkylcarbonyloxy, (C3-C8)-cycloalcényl-(C1-C6)-halogénoalkylcarbonyloxy, (C3-C8)-cycloalcényl-(C1-C6) -alcoxycarbonyloxy, (C3-C8) -cycloalcényl- (C1-C6)-halogénoalcoxycarbonyloxy ;
    - hydroxy-(C1-C6)-alkyle, hydroxy-(C1-C6)-alcoxy cyano- (C1-C6) -alcoxy, cyano- (C1-C6) -alkyle ;
    - (C1-C6) -alkylsulfonyle, (C1-C6) -alkylthio, (C1-C6)-alkylsulfinyle, (C1-C6)-halogénoalkylsulfonyle, (C1-C6) -halogénoalkylthio, (C1-C6)-halogénoalkylsulfinyle, (C1-C6)-alkylsulfonyl-(C1-C6) -alkyle, (C1-C6) -alkylthio- (C1-C6)-alkyle, (C1-C6) -alkylsulfinyl- (C1-C6) -alkyle, (C1-C6)-halogénoalkylsulfonyl-(C1-C6)-alkyle, (C1-C6)-halogénoalkylthio-(C1-C6)-alkyle, (C1-C6)-halogénoalkylsulfinyl-(C1-C6)-alkyle, (C1-C6)-alkylsulfonyl-(C1-C6)-halogénoalkyle, (C1-C6)-alkylthio-(C1-C6)-halogénoalkyle, (C1-C6)-alkylsulfinyl-(C1-C6)-halogénoalkyle, (C1-C6)-halogénoalkylsulfonyl-(C1-C6)-halogénoalkyle, (C1-C6)-halogénoalkylthio-(C1-C6)-halogénoalkyle, (C1-C6)-halogénoalkylsulfinyl-(C1-C6)-halogénoalkyle, (C1-C6)-alkylsulfonyloxy, (C1-C6)-halogénoalkylsulfonyloxy, (C1-C6)-alkylthiocarbonyle, (C1-C6)-halogénoalkylthiocarbonyle, (C1-C6)-alkylthiocarbonyloxy, (C1-C6)-halogénoalkylthiocarbonyloxy, (C1-C6)-alkylthio-(C1-C6)-alkyle, (C1-C6)-alkylthio-(C1-C6)-alcoxy, (C1-C6) -alkylthio- (C1-C6) -alkylcarbonyle, (C1-C6)- alkylthio-(C1-C6)-alkylcarbonyloxy, (C9-C14)-arylsulfonyle, (C6-C14) -arylthio, (C6-C14)-arylsulfinyle, (C3-C8) -cycloalkylthio, (C3-C8)-alcénylthio, (C3-C8)-cycloalcénylthio, (C3-C6)-alcynylthio ;
    - les radicaux R1 et R2 forment ensemble un groupe (C2-C6) -alkylène, qui peut contenir un ou plusieurs atomes d'oxygène et/ou de soufre, le groupe (C2-C6) -alkylène pouvant être monosubstitué ou polysubstitué par halogène et les différents substituants halogène pouvant être identiques ou différents ;
    R3 est choisi dans le groupe constitué par hydrogène, (C1-C6) -alkyle et (C1-C6) -halogénoalkyle ;
    R4 est choisi dans le groupe constitué par (C1-C6)-alkyle, (C1-C6) -halogénoalkyle, hydroxy, (C1-C6)-alcoxy et (C1-C6) -halogénoalcoxy ;
    R5 est choisi dans le groupe constitué par hydrogène, (C1-C6)-alkyle, (C1-C6)-halogénoalkyle, hydroxy, (C1-C6)-alcoxy et (C1-C6)-halogénoalcoxy ;
    R4 et R5, ensemble avec l'atome de carbone auquel ils sont liés, forment un cycle de trois à six chaînons ;
    R6 et R7, à chaque fois indépendamment l'un de l'autre, sont choisis dans le groupe constitué par hydrogène, (C1-C6) -alkyle, (C1-C6) -halogénoalkyle, (C1-C6) -alcoxy, (C1-C6) -halogénoalcoxy, (C6-C14)-aryle, (C6-C14) -aryloxy, (C6-C14) -arylcarbonyle et (C6-C14) -aryloxycarbonyle ; ou les radicaux R6 et R7 forment ensemble un groupe (C2-C7)-alkylène qui peut contenir un ou plusieurs atomes d'oxygène et/ou de soufre, le groupe (C2-C7)-alkylène pouvant être monosubstitué ou polysubstitué par halogène et les différents substituants halogène pouvant être identiques ou différents,
    R8, R9 et R11, indépendamment les uns des autres, sont à chaque fois choisis dans le groupe constitué par hydrogène, halogène, cyano, nitro, (C1-C6)-alkyle, (C1-C6)-alkylcarbonyle, (C1-C6)-alkyloxycarbonyle, (C1-C6) -alkylaminocarbonyle, (C1-C6)-dialkylaminocarbonyle, (C1-C6)-halogénoalkyle, (C1-C6) -alcoxy, (C1-C6)-halogénoalcoxy, (C2-C6)-alcynyle, (C2-C6)-halogénoalcynyle, (C2-C6)-alcynylcarbonyle, (C2-C6)-halogénoalcynylcarbonyle, (C2-C6)-alcynyloxy, (C2-C6)-halogénoalcynyloxy, (C2-C6)-alcynyloxycarbonyle et (C2-C6)-halogénoalcynyloxycarbonyle ; et
    R10 est choisi dans le groupe constitué par halogène, cyano, nitro, (C1-C6)-alkyle, (C1-C6)-alkylcarbonyle, (C1-C6)-alkyloxycarbonyle, (C1-C6)-alkylaminocarbonyle, (C1-C6)-dialkylaminocarbonyle, (C1-C6) -halogénoalkyle, (C1-C6)-alcoxy, (C1-C6)-halogénoalcoxy, (C2-C6)-alcynyle, (C2-C6)-halogénoalcynyle, (C2-C6)-alcynylcarbonyle, (C2-C6)-halogénoalcynylcarbonyle, (C2-C6)-alcynyloxy, (C2-C6) -halogénoalcynyloxy, (C2-C6)-alcynyloxycarbonyle et (C2-C6)- halogénoalcynyloxycarbonyle ; et
    X représente une liaison,
    R12 R13 à chaque fois indépendamment l'un de l'autre, sont choisis dans le groupe constitué par hydrogène, (C1-C6)-alkyle et (C1-C6)-halogénoalkyle ;
    R14 est choisi dans le groupe constitué par hydrogène, (C1-C6)-alkyle, (C1-C6) -halogénoalkyle,
    a) à condition qu'au moins un radical parmi R1, R4, R5, R6, R7, R8, R9, R10 ou R11 soit différent d'hydrogène, lorsque R2 représente CF3,
    b) R2 ne signifie par chlore lorsque R1 représente NH2.
  2. Composés de formule générale (I) selon la revendication 1, caractérisés en ce que le radical R1 est choisi dans le groupe constitué par hydrogène, halogène, cyano, C(=O)NH2, NO2, (C1-C6) -alkyle, (C1-C6)-halogénoalkyle, (C3-C6)-cyclopropyle, (C1-C6)-alcoxy, (C1-C6) -thioalkyle, (C1-C6) -alkylthio, (C2-C6) -alcynyle, mono- (C1-C6) -alkylamino, di- (C1-C6) -alkylamino et tri-(C1-C6)-alkylsilyl-(C2-C6)-alcynyle.
  3. Composés de formule générale (I) selon la revendication 1 ou 2, caractérisés en ce que le radical R2 est choisi dans le groupe constitué par hydrogène, halogène, (C1-C6) -alkylphényle, (C6-C14) -aryle, qui peut être substitué sur le radical aryle par (C1-C6) -alkyle, (C6-C14)-halogénoalkyle et/ou halogène ; C6-aryl-(C1-C6)-halogénoalkyle, (C1-C6) -alkyle, (C1-C6) -halogénoalkyle, (C1-C6)-alcoxy, (C1-C6) -alcoxy- (C1-C6) -alkyle, (C3-C6)- cycloalkyle, qui peut être substitué sur le radical cycloalkyle par (C1-C6)-alkyle, (C6-C14) -halogénoaryle et/ou halogène ; 1-(C1-C6)-alkylcyclopropyle, 1-((C1-C6)-alkyl-C6-aryl)-cyclopropyle, 1-(monohalogénophényl)-cyclopropyle, 1-(dihalogénophényl)-cyclopropyle, mono-(C1-C6) -alkylamino, di- (C1-C6)-alkylamino, (C1-C6)-thioalkyle, (C1-C6)-alkylthio, (C1-C6)-alcoxy et amino.
  4. Composés de formule générale (I) selon la revendication 1, caractérisés en ce que R1 et R2, ensemble avec les atomes de carbone, auxquels ils sont liés, forment un cycle de cinq ou six chaînons, qui peut être interrompu par un ou deux hétéroatomes, choisis dans le groupe constitué par oxygène et soufre.
  5. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 4, caractérisés en ce que le radical R3 représente hydrogène ou (C1-C6)-alkyle.
  6. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 5, caractérisés en ce que le radical R4 est choisi dans le groupe constitué par (C1-C6)-alkyle, hydroxy, cyclopropyle et (C1-C6)-alcoxy et le radical R5 est choisi dans le groupe constitué par hydrogène, (C1-C6)-alkyle, hydroxy, cyclopropyle et (C1-C6)-alcoxy.
  7. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 5, caractérisés en ce que les radicaux R4 et R5 forment ensemble un groupe (C1-C7)-alkylène, qui peut contenir un ou plusieurs atomes d'oxygène et/ou de soufre, le groupe (C1-C7)-alkylène pouvant être monosubstitué ou polysubstitué par halogène et les différents substituants halogène pouvant être identiques ou différents.
  8. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 7, caractérisés en ce que les radicaux R6 et R7, indépendamment l'un de l'autre, sont choisis dans le groupe constitué par hydrogène, (C1-C6)-alkyle et (C6-C14)-aryle.
  9. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 8, caractérisés en ce que le radical R8 est choisi dans le groupe constitué par hydrogène, (C1-C6)-alkyle et halogène.
  10. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 9, caractérisés en ce que le radical R9 est de préférence choisi dans le groupe constitué par hydrogène et (C1-C6)-alkyle.
  11. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 10, caractérisés en ce que le radical R10 est choisi dans le groupe constitué par (C1-C6)-alkyle, di-(C1-C6)-alkylamino, ) halogène, (C2-C6) -alcényle, (C2-C6) -alcynyle, (C1-C6)-alkyl- (C2-C6) -alcynyle, (C1-C6) -alcoxy- (C1-C6) -alkyl- (C2-C6)-alcynyle, cyano, (C1-C6)-alcoxycarbonyle et aminocarbonyle.
  12. Composés de formule générale (I) selon l'une quelconque des revendications 1 à 11, caractérisés en ce que R11 est choisi dans le groupe constitué par hydrogène et (C1-C6)-alkyle.
  13. Procédé pour la préparation de composés optiquement actifs de formule générale (I)
    Figure imgb0036
     les radicaux R1 à R11 et X présentant les significations selon l'une quelconque des revendications 1 à 12, caractérisé en ce qu'on transforme
    (1) un composé de formule générale (II)
    Figure imgb0037
     dans laquelle R1 et R2 présentent une signification selon l'une quelconque des revendications 1 à 11 et Z1 signifie un radical pouvant être échangé ou un groupe partant, tel qu'en particulier chlore, trichlorométhyle, (C1-C4)-alkylsulfonyle, phényl-(C1-C4)-alkylsulfonyle ou (C1-C4)-alkylphénylsulfonyle substitué ou non substitué, avec une amine de formule générale (III) ou un sel d'addition d'acide correspondant.
    Figure imgb0038
  14. Agent herbicide ou de régulation de la croissance de plantes, caractérisé en ce qu'il contient un ou plusieurs composés de formule générale (I) ou leurs sels selon l'une quelconque des revendications 1 à 12.
  15. Procédé pour lutter contre des plantes nuisibles ou pour la régulation de la croissance de plantes, caractérisé en ce qu'on applique une quantité active d'un ou de plusieurs composés de formule générale (I) ou de leurs sels selon l'une quelconque des revendications 1 à 12 sur des plantes, des parties de plantes, des graines de plantes ou sur une surface de culture.
  16. Utilisation de composés de formule générale (I) ou de leurs sels selon l'une quelconque des revendications 1 à 12 comme herbicides ou régulateurs de la croissance de plantes.
  17. Utilisation selon la revendication 16, caractérisée en ce que les composés de formule générale (I) ou leurs sels sont utilisés pour lutter contre des plantes nuisibles ou pour la régulation de la croissance de plantes dans des cultures de plantes utiles ou décoratives.
  18. Utilisation selon la revendication 17, caractérisée en ce que les plantes de culture sont des plantes de culture transgéniques.
  19. Utilisation selon la revendication 17 ou 18, caractérisée en ce que les plantes de culture sont choisies parmi les cultures en plantation.
EP09799289.5A 2008-12-30 2009-12-28 Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes Active EP2384322B1 (fr)

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EP2210879A1 (fr) * 2008-12-30 2010-07-28 Bayer CropScience AG Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes
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EP2384322A1 (fr) 2011-11-09
US20100167935A1 (en) 2010-07-01
BRPI0923893A2 (pt) 2020-08-11
JP2012514016A (ja) 2012-06-21
MX2011006278A (es) 2011-06-24
EP2206703A1 (fr) 2010-07-14
CN102272107A (zh) 2011-12-07
KR20110102482A (ko) 2011-09-16
WO2010076009A1 (fr) 2010-07-08
WO2010076009A8 (fr) 2011-06-23
AR074921A1 (es) 2011-02-23
BRPI0923893B1 (pt) 2021-03-09
JP5826633B2 (ja) 2015-12-02
US8445408B2 (en) 2013-05-21
TW201034572A (en) 2010-10-01
CA2748577A1 (fr) 2010-07-08
CN102272107B (zh) 2015-10-14

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